Pyrrolidine → 3-Amino-4-(1-pyrrolidinylmethyl)benzoic acid

HRID 248709

반응식

HRID 248709 반응식
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>ClCCl>[NH2:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH2:2][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7]([OH:9])=[O:8]

참가 물질

4

반응물 2

HCID 31268PyrrolidineHCID 1323864-Bromomethyl-3-nitrobenzoic acid

생성물 1

HCID 156703753-Amino-4-(1-pyrrolidinylmethyl)benzoic acid수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Bromomethyl-3-nitrobenzoic acid (10 g) is dissolved in dichloromethane (100 ml) and thereto is added dropwise pyrrolidine (8 g) with stirring under ice cooling, and the mixture is stirred at room temperature for 30 minutes. Dichloromethane is distilled off under reduced pressure, and the residue is dissolved in conc. hydrochloric acid (40 ml) and thereto is added water (10 ml) with stirring under ice cooling and further is added tin (5.4 g), and the mixture is stirred under ice cooling for 1.5 hour. The reaction mixture is neutralized with 10N aqueous sodium hydroxide solution, and the catalyst is filtered off and the filtrate is concentrated. The residue is dissolved in water and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected, and concentrated into dryness under reduced pressure to give 3-amino-4-(1-pyrrolidinylmethyl)benzoic acid (7.2 g).

후처리

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. distillationDichloromethane is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in conc. hydrochloric acid (40 ml)
  4. additionis added water (10 ml)
  5. stirringwith stirring under ice cooling
  6. additionfurther is added tin (5.4 g)
  7. stirringthe mixture is stirred under ice cooling for 1.5 hour
  8. filtrationthe catalyst is filtered off
  9. concentrationthe filtrate is concentrated
  10. dissolutionThe residue is dissolved in water
  11. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  12. additionThe fractions containing the desired compound
  13. customare collected
  14. concentrationconcentrated into dryness under reduced pressure

출처 및 근거

ORD 기록
ord-e4f1c9c80e1c41b1a0032d693db6c0e1
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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